Water ethylacetate → 5-[3-(4-Fluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester

HRID 1962986노트

반응식

HRID 1962986 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[N:16][O:17][C:18]=2/[CH:19]=C/C2C=CC=CC=2)=[CH:8][N:7]=1)=[O:5])[CH3:2].I([O-])(=O)(=O)=[O:35].[Na+].C(OCC)(=O)C.O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)=[N:16][O:17][C:18]=2[CH:19]=[O:35])=[CH:8][N:7]=1)=[O:5])[CH3:2]

참가 물질

8

반응물 3

HCID 22728543Water ethylacetateHCID 23667635Sodium periodateHCID 666444395-[3-(4-Fluoro-phenyl)-5-((E)-styryl)-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester

생성물 1

HCID 866472865-[3-(4-Fluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester수율 72%

시약·촉매·용매 4

HCID 30318Osmium Tetroxide촉매HCID 66133Benzyl triethylammonium chloride촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 5-[3-(4-fluoro-phenyl)-5-((E)-styryl)-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester (2.0 g, 4.5 mmol), osmium(VIII) oxide (28.6 mg, 0.11 mmol), sodium metaperiodate (3.85 g, 18 mmol), benzyltriethylammonium chloride (418 mg, 1.8 mmol) in dioxane (30 mL) and water (10 mL) was irradiated in the microwave for 15 min at 120° C. Extractive workup (ethyl acetate/water) was followed by drying of the organic phase over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate=4:1 to 1:1) afforded the title compound (1.2 g, 72%) as a colourless gum. MS: m/e=371.1 [M+H]+.

후처리

  1. customwas irradiated in the microwave for 15 min at 120° C
  2. dry with materialby drying of the organic phase over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by chromatography (silica, heptane:ethyl acetate=4:1 to 1:1)

출처 및 근거

ORD 기록
ord-52e6c413ae234b8ba4622675bb79422a
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415379B2

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